Acetic Acid → ethyl 5-{(2RS,3SR)-3-hydroxy-2-(4-nitrophenyl)butyl}-2-furancarboxylate

HRID 850658Notes

Reaction equation

HRID 850658 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:22](=[O:24])[CH3:23])[CH2:11][C:12]2[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].O.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[OH:24][CH:22]([CH3:23])[CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH2:11][C:12]1[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3611392Lithium tri-s-butylborohydrideHCID 15458175Ethyl 5-(2-(4-nitrophenyl)-3-oxobutyl)-2-furancarboxylate

Product 1

HCID 19364506ethyl 5-{(2RS,3SR)-3-hydroxy-2-(4-nitrophenyl)butyl}-2-furancarboxylateYield 66.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

5.48 g of ethyl 5-{2-(4-nitrophenyl)-3-oxobutyl}-2-furancarboxylate was dissolved in 50 ml of tetrahydrofuran, and 16.5 ml of a 1M tetrahydrofuran solution of lithium tri-sec-butylborohydride was added under cooling to -78° C. with stirring, followed by stirring at the same temperature for 2 hours. Water as added to the reaction solution, followed by stirring at room temperature for 30 minutes. Then, the solution was acidified by an addition of acetic acid. Ethyl acetate was added thereto for extraction. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→1/1) to obtain 3.66 g of the above-identified compound.

Workup

  1. stirringby stirring at the same temperature for 2 hours
  2. stirringby stirring at room temperature for 30 minutes
  3. extractionfor extraction
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→1/1)

Sources & evidence

ORD record
ord-4ca5b1556f314bba90555e9830571f02
Source dataset
uspto-grants-2000_01
Patent number
US06017956

Reaction notes

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